Ch22. Organic Compounds, Polymers, and Biochemicals

Ch 22.
Organic Compounds,
Polymers,and Biochemicals
Brady & Senese, 5th Ed.
Index
22.1. Organic chemistry is the study of carbon compounds
22.2. Hydrocarbons consist of only C and H atoms
22.3. Ethers and alcohols are organic derivatives of water
22.4. Amines are organic derivatives of ammonia
22.5. Organic compounds with carbonyl groups include aldehy
des, ketones, and carboxylic acids
22.6. Polymers are composed of many repeating molecular
units
22.7. Most biochemicals are organic compounds
22.8. Nucleic acids carry our genetic information
Organic Compounds Are Diverse

Carbon compounds are greatly variant due to the
properties of C:
C is able to bond multiply

C is able to catenate
C is able to bond with a wide variety of elements
Isomers are possible when there is a carbon chain
Combinations of functional groups give great diversity
Carbon can form rings
Carbon Compounds
Carbon containing compounds exist in large
variety, mostly due to the multiple ways in which
C can form bonds
Some groups of atoms with similar bonding are
commonly seen, called functional groups.
Molecules may contain more than one functional
group
Can form chiral compounds
VSEPR Structures
Show all atoms
Show attachments between atoms but not how many
pairs of electrons were used
Show the geometric arrangement of the atoms
H H H
H H
H
C
C
H
H H
Condensed Structures
show the general arrangement of the atoms and the
number of atoms
no effort is made to indicate geometry, types of bonds,
or lone pairs
CH3CH2CH2CH2CH3
Alcohols & Ethers Are Polar

Contain C, H, and O, all with single bonds.
Alcohols end in OH (R-OH)
Ethers have an O atom in the chain (R-O-R)
The Carbonyl Group

When C in a chain has a double bond to an oxygen, the
group is termed a carbonyl
Aldehydes, ketones, carboxylic acids, and amides all
contain carbonyl groups
RC H
R C R'
R C OH
aldehyde
ketone
carboxylic acid
||
||
O
||
Aldehydes & Ketones Are Polar

Each has a carbon chain terminating in a carbonyl.
Aldehydes then have an added H (RCOH)
Ketones have another carbon chain (RCOR)
Amines & Amides Are Polar

Amines contain -NH2 on carbon chain (RNHR)
Amides contain NH2 on carbon chain with
carbonyl (RCONH2)
10
Carboxylic Acids & Esters Are Polar

Both have a carbon chain terminating in a
carbonyl
Carboxylic acids then have an OH group
A combined carbonyl and hydroxyl group form a
carboxyl group (RCOOH)
Esters then have a singly bound O, then another
carbon chain (RCOOR)
11
Identify The Functional Groups Present
12
Using Functional Groups

Collecting molecules into families means that only
a few kinds of reactions must be learned
The emphasis is on the properties of the functional
group, not individual molecules
Once the center of reactivity is identified, its
characteristic reactions are expected to occur
13
Functional Groups And Their Properties

Polar functional groups contain O and N
Like dissolves like: polar solvents will dissolve
the polar functional groups
As the carbon chain increases in size, the polarity
decreases
14
Your Turn!
Which of the following
contains an amide
group?
A. The top structure
B. The middle
structure
C. The bottom
structure
D. None of these
15
Lewis Structures Of Hydrocarbons

Show all atoms, and all electrons
Bond pairs usually shown as a line
Non-bonding (lone) pairs of electrons are shown
as dots
H H H H H
H C C C C C H
H H H H H
16
Stick Figures
Each vertex and terminus is a carbon
Assumes that the termini contain as many H as
needed for saturation of the C
(hydrogens attached to hetero-atoms are shown)
All hetero-atoms are shown explicitly

Double bonds explicitly shown
H
H
H
H
H
H
C
C
C
H
C
C
H
H H H H
17
Learning Check
Fill in the missing atoms and derive the condensed
structure
O
O
C5H12
C4H8O2
18
Your Turn!
Which is the correct formula for the structure
shown?
A. C42H12
B. C24H12
C. C36G12
D. None of these
19
Alkanes & Alkenes Are Non-polar

Alkanes are hydrocarbons (contain only C and H)
have a ratio of atoms CnH2n+2
Alkenes- hydrocarbons with fewer H than the

alkanes (CnH2n)
Use the same prefixes, but have the suffix -ene.
20
Alkanes (CnH2n+2)
Composed of hydrocarbon chains in which carbons
are attached to one another by single bonds
Are named by the number of C in the chain and
where any substitutions are found
Prefixes and the associated numbers of carbon
atoms
meth-1
eth-2
prop-3
but-4
pent-5
hex-6
hept-7
oct-8
non-9
dec-10
21
Naming Alkanes
1. Find the longest continuous chain of carbons-the root.
2. a. Name the root by adding -ane to the appropriate

prefix (a 4-carbon chain would be butane)
b. Identify any branches, and name each by the
number of carbons (a 1-carbon branch is methyl-)
3. a. List side chains in alphabetical order, before the
root
b. Use di, tri, tetra (etc) if you have more than one
of something (these do not count in alphabetizing)
22
Naming (Cont.)
4. Number root from side closest to the first
branch
5. Use numbers to tell where the side chains
sprout from the root
6. Put a dash between any number and letter or
any letter and number. Use a comma between
two numbers
7. Use the prefix cyclo for ring systems
23
Name the following
3-ethyl-2-methylhexane
2,3,3,4-tetramethylhexane
3-methylheptane
3-ethyl-4-methylhexane
24
Your Turn!
Name the structure shown:
A. 1,2-dimethylpentane
B. 3-methylhexane
C. 2-ethylpentane
D. None of these
25
Reactions Of Alkanes
Alkanes are generally stable at room temperature
They burn in air to given carbon dioxide
When heated at high temperature they crack (break into
smaller molecules)
CH 4 high
tempe rature
C 2H 2
CH 3CH 3 high
tempe rature
H 2 C CH 2 H 2
ethane
ethene
26
Unsaturated Hydrocarbons
Hydrocarbons with one or more double bonds are
members of the alkene family
open chain alkenes have the general formula C2H2n
Hydrocarbons with triple bonds are in the alkyne

family
open chain alkynes have the general formula, CnH2n2
27
Naming Alkenes
The parent chain must include the double bond
The parent alkene chain must be numbered from
whichever end gives the first carbon of the double
bond the lowest number
This number, followed by a hyphen, precedes the
name of the parent chain, unless there is no
ambiguity about where the double bond occurs
The locations of branches are not a factor in
numbering the chain
Alkyl groups are named and located as before
28
Name The Following
ethylene
2,3-dimethyl-1-pentene
29
Your Turn!
Which name is not correct?
A.
3-pentene
B.
2-pentene
C.
2-methyl-1-butene
D. All are correct

30
Geometric Isomers
Cis and trans isomers exist when there
is a plane of a double bond or of a
ring structure
cis same
trans-opposite
31
Your Turn
Which isomer is shown:
A. cisB. transC. cant tell
32
Addition Reactions of Alkenes

Alkenes undergo addition reactions that eliminate the
pi-bond
CH2=CH2 + HCl(g) Cl- CH2-CH3
Inorganic compounds that undergo addition reactions

with alkenes include: H2O, Cl2, Br2, I2, and H2.
Ozone (O3) reacts with anything that has a carboncarbon double or triple bond, forming a variety of
products
33
Aromatic Compounds
Contain a benzene(C6H5-) ring with delocalized
electrons
Aromatic compounds undergo substitution reactions
instead of addition reactions because of the
resonance energy of the ring
example: C6H6 + Cl2C6H5Cl + HCl
34
Ethers (ROR)
Result when both hydrogen atoms in water are
replaced with alkyl groups
Are almost as chemically inert as alkanes: they
burn and are split apart when boiled in
concentrated acid
Are named by naming each alkyl group,
alphabetically, and end with ether
Learning Check:
CH3OCH3
CH3CH2OCH3
CH3CH2OCH2CH3
dimethyl ether
ethyl methyl ether
diethyl ether
35
Alcohols (ROH)
When an alkyl group replaces a hydrogen in water, an
alcohol results
The name ending for alcohols is ol
The parent chain must include the carbon containing the
OH group
Learning Check: Name the following
CH3CH2OH
CH3CH2CH2CH2OH
ethanol
butanol
36
Oxidation of Alcohols
If the alcohol carbon atom holds at least one H atom, it
can be replaced with bonds to oxygen
O
RCH 2OH
alcohol
Further
oxidation
||
R CH
oxidation
aldehyde
O
||
||
R C OH
carboxylic acid
Further
oxidation
CH 3CH 2OH oxidation

CH 3 C H
O
||
CH 3 C OH
37
Dehydration Of Alcohols:
The reverse the the addition of water to an
alkene, it is an example of an elimination
reaction
CH 3 C H C H 2 CH 3CH CH 2 H 2O
|
OH
22.3.Ethers and alcohols are organic derivatives of water
38
Substitution Reactions Of Alcohols

Under acidic conditions, the -OH group can be
replaced by a halogen atom
CH 3CH 2CH 2OH HBr(conc) CH 3CH 2CH 2 Br H 2O
1 - propanol
1 - bromopropane
39
Your Turn!
What type of structure is shown
A. Alcohol
B. Ether
C. Peroxide
D. aldehyde
40
Amines
Are derivatives of ammonia where one or more
hydrogens have been replaced with alkyl groups
NH3 is ammonia
CH3NH2 is methylamine
(CH3)2NH is dimethylamine and (CH3)3N is
trimethylamine (bp 3oC).
Amines are bases, and react with strong proton

donors to form ammonium ion-like structures
NH 3 (aq) H (aq) NH 4 (aq)
CH 3CH 2 NH 2 (aq) H (aq) CH 3CH 2 NH 3 (aq)

41
Protonated Amines
Are more soluble in water than amines
Protonated amines (like protonated ammonia) are weak
acids that can react with base
NH 4 (aq) OH (aq) NH 3 (aq) H 2O
CH 3CH 2 NH 3 (aq) OH (aq) CH 3CH 2 NH 2 (aq) H 2O
42
Aldehydes
The IUPAC name ending for an aldehyde is al
The parent chain is the longest chain that includes
the aldehyde group
22.5. Organic compounds with carbonyl groups include aldehydes, ke 43
Ketones
The IUPAC ending for ketones is one.
The parent chain must include the
carbonyl group
propanone 3-pentanone
Reactions Of Aldehydes & Ketones

Aldehydes and ketones can be hydrogenated to
give alcohols
O
||
CH 3CH 3 C H H 2 CH 3CH 2 CH 2OH

O
||
1 - propanol
OH
|
CH 3 C CH 3 H 2 CH 3 C H CH 3
2 - propanol
Aldehydes undergo oxidation to form

carboxylic acids, while ketones strongly resist
oxidation
Carboxylic Acids
The IUPAC name ending for carboxylic acids is
oic acid. the parent chain must include the
carbonyl carbon, which is numbered as position 1
The common names are used for these: formic

acid and acetic acid
Your Turn!
Which of the following contain a carbonyl group?
A. amine
B. amide
C. carboxylic acid
D. All contain a carbonyl
Esters
In esters, the OH of the carboxyl group is
replaced by -OR
Name the alkyl group attached to the O atom
followed by a separate word generated from
the name of the parent acid by changing oic
acid to -ate
methyl methanoate
ethyl ethanoate
Preparation Of Esters
Esters can be prepared by heating the parent acid with
an alcohol in the presence of an acid catalyst
O
||
||
R C OH HOR' R C OR' H 2O
O
||
||
CH 3 CH 2 C OH HOCH 2CH 3 CH 3 CH 2 C OCH 2CH 3 H 2O

ethanoic acid
ethanol
ethyl ethanoate
Reactions of Esters
Carboxylic acids and alcohols can be obtained by
heating esters with acid in a large excess of water
Esters are split apart by the action of base in a reaction
called saponification
O
||
CH 3 CH 2 C OCH 2CH 3 (aq ) NaOH (aq)
heat
ethyl ethanoate
O
||
CH 3 CH 2 C O (aq ) Na (aq ) CH 3CH 2OH

ethanoate ion
ethanol
Amides (RCONH2)
Carboxylic acids can also be converted into amides, a
functional group found in proteins
Simple amides are those in which the nitrogen bears
no alkyl groups, only hydrogen atoms
The IUPAC names of simple amides are generated by
replacing the oic acid of the parent carboxylic acid
with -amide
H2N
O
NH2
propanamide
2-methyl-butanamide
Preparation of Amides
One way to prepare simple amides is by heating
a carboxylic acid in excess ammonia
O
||
R C OH NH 3
heat
||
R C NH 2 H 2O
O
||
CH 3CH 2 C OH NH 3
propanoic acid
heat
||
CH 3CH 2 C NH 2 H 2O
propanamide
Reactions of Amides
Amides, like esters, can be hydrolyzed
O
||
R C NH 2 H 2O
heat
||
R C OH NH 3
O
||
CH 3CH 2 C NH 2 H 2O
propanamide
heat
||
CH 3CH 2 C OH NH 3
propanoic acid
Amides are not bases; the O on the carbonyl draws

electron density to itself and tightens the unshared
electrons on N, preventing their donation
Your Turn!
Which of these can be hydrolyzed (react with water)
A. amides
B. alkanes
C. alcohols
D. None of these
Polymers
Are large molecules with repeating units called
monomers
22.6. Polymers are composed of many repeating molecular units
55
Formation Of Addition Polymers

Initiators attack a monomer and make it receptive
for the new bond
Addition polymers are assembled from molecular

units that combine to form one larger molecule
56
Addition Polymer: Polystyrene

Styrene is treated with an initiator to form a free
radical
Radical end is free to form a new connection to
another styrene molecule
57
Formation Of Condensation Polymers

Condensation polymers are formed when monomers
add and lose a small molecule
adipic acid and hexamethylene diamine combine
and eliminate water to form Nylon 6,6
The ends are free to continue the process
58
Crosslinking
Branches on polymers
make them susceptible
to interaction with other
polymers
Increased crosslinking
leads to increased
strength
The concept behind
vulcanized rubber
59
Learning Check: Teflon

Is formed from the monomer F2CCF2 . Based on
the structure of polytetrafluoroethylene (PFTE), is
this an addition or a condensation polymer?
addition
60
The Polyethylenes: LDPE, HDPE and

UHMWPE
Have widely disparate
properties due to the degree of
order
low density (LD) PE with an
unordered crystal, is used for
grocery sacks
high density (HD) PE with
highly structured crystal is
very strong and used in
TYVEK
ultra-high molecular weight
(UHMW) PE has very long
HDPE fibers and is used in
bulletproof vests and sails
61
Your Turn!
One form of Gak can be made by combining
dissolved white glue and dissolved borax
powder. What characteristics would you expect
if the amount of cross-linker (the borax) is
increased in the blend?
A. It becomes more viscous
B. It becomes more solid
C. It tears rather than stretches
D. All of the above
62
Biochemistry
The systematic study of the chemicals of living things
A variety of compounds are required for cells to work:
lipids
carbohydrates
proteins
nucleic acids
63
Carbohydrates
Are naturally occurring polyhydroxyaldehydes or
polyhydroxyketones, or else compounds that react
with water to give these
Types:
monosaccharides
disaccharides
polysaccharides
64
Monosaccharides
Are carbohydrates that do not react with water
The most common monosaccharide is glucose
(pentahydroxyaldehyde)
glucose is the chief carbohydrate in blood, and provides
a building units for polysaccharides like cellulose and
starch
OH
OH
OH
H2C H C H C
C H C H CH
OH OH O
H2
HO
C OH
HC CH
HO CH
O
HC CH
OH
HO
glucose (open chain polyhydroxyaldehyde)
-glucose
65
Disaccharides
Are carbohydrates that split into two
monosaccharide molecules by reacting with water
example: sucrose (table sugar, cane sugar, or beet
sugar) which gives glucose and fructose upon
hydrolysis
66
Polysaccharides
Are naturally occurring polymers whose molecules
involve thousands of monosaccharide units linked to
each other by oxygen bridges
include starch, glycogen, and cellulose -all give only
glucose upon hydrolysis
plants store energy as starch
the hydrolysis of amylose (the simplest starch) can be
represented as:
Glu (O Glu ) n OH nH 2O n glucose
amylose (n is large)
67
Storage of glucose
Animals store glucose for energy as glycogen
excess glucose is converted to glycogen by liver and
muscle cells and stored for later use
Cellulose, a chief component of plant cell walls,

is a polymer of glucose that requires a special
enzyme to hydrolyze
humans lack this enzyme and so are unable to use
cellulose for food
cellulose is the fiber found in foods like lettuce
68
Lipids
Are fats and oils that are non-polar, so they do not
dissolve in water
Are amphipathic:
the purely hydrocarbon-like portions (the long R groups
contributed by the fatty acids) avoid water and are
called hydrophobic or water fearing
the polar heads are hydrophilic or water loving
69
Triacylglycerols
Are esters between glycerol and include
edible fats and oils like olive oil, butterfat,
and lard
Are called vegetable oils when derived
from plants and animal fats when derived
from animals, and are made from fatty
acids
Are said to be polyunsaturated; vegetable
oils tend to have more alkene double
bonds per molecule than animal fats
70
Glycerophospholipids
The lipids involved in animal cell membrane are called
glycerophospholipids
The lipid molecules of animal cell membranes are organized as a bilayer.

71
Your Turn!
Which are forms of fats?
A. Lipids
B. Glycerols
C. Polysaccharides
D. All of these
72
Proteins
The dominant structural units of proteins are
macromolecules called polypeptides
polypeptides are made from a set of about 20
monomers called amino acids
polypeptides are copolymers of the amino acids
73
Reactions of Proteins
The final shape of a protein, called its native
form, is critical to its ability to function
Physical agents such as heat, poisons, and certain
solvents can alter a proteins native form
when this happened the protein is said to have been
denatured
Enzymes are the catalysts in living cells

Virtually all enzymes are proteins
74
Nucleic Acids
Carry the genetic
code
Are made of amino
acids
75
Reactions of DNA
The best hydrogen bonds are formed when the base
pairs that makeup the backbone match
Adenine (A) pairs with thymine (T), cytosine (C) pairs with
guanine (G), etc
DNA replicates itself by splitting the parent DNA

double helix and assembling the matching base pairs
on each strand
The result is two daughter DNA double helixes
76
Replication of DNA
77
DNA Characteristics
A single human gene has between 1000 and
3000 bases
the bases do not occur continuously on a DNA
molecule
the separated segments of a DNA chain that make up
a gene are called exons because that unit helps to
express a message
the sections of DNA between the exons are called
introns because they are units that interrupt the gene
78
Preparation of Polypeptides
Each polypeptide in a cell is made under the direction
of its own gene
The production of a polypeptide can be represented as:
DNA transcript
ion RNA translatio
n polypeptide
Transcription: the genetic message is read off in the cell

nucleus and transferred to ribonucleic acid (RNA)
Translation: the genetic message, now on RNA outside the
nucleus, is used to direct the synthesis of a polypeptide
79
RNA
Four types of RNA are involved in the connection of
the gene to the polypeptide
ribosomal RNA or rRNA is packed together with enzymes
in ribosomes, the manufacturing stations for polypeptides.
messenger RNA or mRNA brings the blueprints for
particular polypeptide to the manufacturing station
(ribosome)
heterogeneous nuclear RNA or hnRNA carries the
prefabricated parts (amino acids) to the ribosome
transfer RNA or t-RNA carries amino acids to the
ribosomes
80
Genetic Defects
About 2000 diseases are attributed to various
kinds of defects in the genetic machinery of
cells
if a single base is wrong in a gene, it could result in
a completely different polypeptide being produced,
possibly with fatal consequences
Atomic radiation and chemical agents can also

cause defects, possibly causing cancer
81
Viruses
Viruses are packages of chemicals usually
consisting of nucleic acid and protein
Their nucleic acid takes over the genetic
machinery in certain cells of the host tissues
causing them to manufacture more virus particles
The host cell bursts, releasing the newly
manufactured viruses, which can infect more cells
82
Your Turn!
How many types of RNA are there in a living
organism?
A. 1
B. 2
C. 3
D. 4
83
Your Turn!
How many types of DNA are there in a living
organism?
A. 1
B. 2
C. 3
D. 4
84

Ch22. Organic Compounds, Polymers, and Biochemicals

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Ch22. Organic Compounds, Polymers, and Biochemicals

Uploaded by

Copyright:

Available Formats

Ch 22.

Brady & Senese, 5th Ed.

Organic Compounds Are Diverse

C is able to bond multiply

22.1. Organic chemistry is the study of carbon compounds

22.1. Organic chemistry is the study of carbon compounds

22.1. Organic chemistry is the study of carbon compounds

22.1. Organic chemistry is the study of carbon compounds

Alcohols & Ethers Are Polar

22.1. Organic chemistry is the study of carbon compounds

The Carbonyl Group

22.1. Organic chemistry is the study of carbon compounds

Aldehydes & Ketones Are Polar

22.1. Organic chemistry is the study of carbon compounds

Amines & Amides Are Polar

22.1. Organic chemistry is the study of carbon compounds

Carboxylic Acids & Esters Are Polar

22.1. Organic chemistry is the study of carbon compounds

Identify The Functional Groups Present

22.1. Organic chemistry is the study of carbon compounds

Using Functional Groups

22.1. Organic chemistry is the study of carbon compounds

Functional Groups And Their Properties

22.1. Organic chemistry is the study of carbon compounds

22.1. Organic chemistry is the study of carbon compounds

Lewis Structures Of Hydrocarbons

All hetero-atoms are shown explicitly

22.2. Hydrocarbons consist of only C and H atoms

Alkanes & Alkenes Are Non-polar

Alkenes- hydrocarbons with fewer H than the

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

2. a. Name the root by adding -ane to the appropriate

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

Name the following

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

Hydrocarbons with triple bonds are in the alkyne

22.2. Hydrocarbons consist of only C and H atoms

Name The Following

22.2. Hydrocarbons consist of only C and H atoms

D. All are correct

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

Addition Reactions of Alkenes

Inorganic compounds that undergo addition reactions

22.2. Hydrocarbons consist of only C and H atoms

22.2. Hydrocarbons consist of only C and H atoms

22.3. Ethers and alcohols are organic derivatives of water

22.3. Ethers and alcohols are organic derivatives of water

CH 3CH 2OH oxidation

22.3. Ethers and alcohols are organic derivatives of water

22.3.Ethers and alcohols are organic derivatives of water

Substitution Reactions Of Alcohols

22.3. Ethers and alcohols are organic derivatives of water

22.3. Ethers and alcohols are organic derivatives of water

Amines are bases, and react with strong proton

CH 3CH 2 NH 2 (aq) H (aq) CH 3CH 2 NH 3 (aq)

22.4. Amines are organic derivatives of ammonia

22.5. Organic compounds with carbonyl groups include aldehydes, ke 43

22.5. Organic compounds with carbonyl groups include aldehydes, ke 44